World Ventures Incorporated

Brad Flora, known in Chicago as the founder of media site Windy Citizen, has failed, pivoted and moved to Silicon Valley. And this week, he sold his latest company, NowSpots Inc., the creator of Perfect Audience, for $25.5 million. “This is the first time when the end of the road wasn’t me turning off the servers,” said Flora, who shuttered Windy Citizen in 2012. “It feels great.” Flora came to the Chicago area in 2006 to pursue a graduate degree that would propel him into media entrepreneurship with Windy Citizen and other projects that made their mark but eventually failed. In May 2011, Flora and his co-founder at the time moved to Mountain View,...